Itinerary: 2 weeks in Italy

Planning an itinerary for two weeks in Italy is exciting and overwhelming. Where do you start?

In the north, the fashion & finance powerhouse of Milan, the sinking canals of Venice and the bright villages of Cinque Terre each demand attention.

The olive groves and vineyards of Tuscany, the streets of Florence oozing Renaissance splendour and the fine foods of Emilia-Romagna tempt travellers in the centre.

In the south, the Italian Riviera towns of Positano, Amalfi and Capri,  the gritty, history-soaked streets of Rome and the sunny seaside towns in Campania pack a punch.

The country is rich in history, culture and of course, food & wine that makes gourmands and gourmets alike weak at the knees, the world over.

Boboli Gardens view Florence Duomo

Italy unified in the late 19th century, yet many Italians do not in fact, consider themselves Italians: They are Romans, they are Sicilians, they are Milanese, they are Venetian.

Despite being unified under one white, red and green banner, the country is a patchwork of diverse regional cultures and treasures. So many wonderful, enticing destinations makes planning a trip to Italy overwhelming – and exciting!

I get a lot of questions about my itineraries, so today I’m sharing how I spent two weeks in Italy, during five weeks travelling from Paris to Athens.

I was travelling with my best friend on this trip, who had never visited Europe before. This was my third trip to Europe, and second trip to Italy, so we visited places I’d seen before and some that were new to me.

In two weeks, we met our goal of spending times in a variety of cities and small towns and seeing a handful of iconic places, with some lesser-known spots thrown in too.

2 weeks in Italy travel route map

2 Weeks in Italy Itinerary

  • Cinque Terre (3 nights)
  • Milan (stop over)
  • Verona (2 nights)
  • Venice (day trip)
  • Florence (3 nights)
  • Rome (3 nights)
  • Sorrento (2 nights)
  • Amalfi & Positano (day trip)
  • Capri (day trip)
  • Pompeii (day trip)
  • Bari – Overnight ferry to Greece!

Levanto, Cinque Terre (2 nights)

For centuries, the five villages of Cinque Terre were a secret to all but the villagers who lived there – and the occasional pirate.

Dotted along 18km of coastline between Genoa and La Spezia on Italy’s Ligurian coast, the mountains created a natural barrier between Cinque Terre and the rest of the world.

The villages only became accessible by rail in the 19th century and are still inaccessible by car. The introduction of the railway led to locals migrating into other parts of Italy and all but abandoning the traditional way of life.

Colourful Building in Riomaggiore Cinque TerreChurch and flags in Riomaggiore Cinque Terre

In the 1970s, tourism changed Cinque Terre forever. Once the secret was out, it rocketed to the top of many traveller’s lists. With an influx of tourism, also came opportunities for locals to stay in Cinque Terre and earn a living.

Fortunately, the towns became part of Italy’s first national park in 1999, in Parco Nazionale delle Cinque Terre.

From north to south the villages are Monterosso al Mare, Vernazza, Corniglia, Manarola and Riomaggiore. Corniglia is the only one inaccessible by sea, perched high on a rocky outcrop.

Highlights in Levanto

We stayed in Levanto for the first couple of nights, which is a small seaside town, 10 minutes by train from the northernmost CT village, Monterosso.

From Levanto, we did day trips to two Cinque Terre villages, Monterosso and Vernazza.

To be honest, I’m not really sure why I decided to book in Levanto instead of a Cinque Terre village. I probably thought it would be cheaper, or maybe everything was booked out. Either way, I’m so glad I did!

Levanto Italy

We didn’t know what to expect when we arrived in Levanto, but we found a relaxed seaside community. We heard Italian being spoken everywhere we went, and rarely saw other travellers, apart from a couple who got lost looking for Cinque Terre.

Cinque Terre villages are so small, that they are easily overwhelmed by tourists. Levanto is off the tourist trail and it’s just big enough that it feels like there is a strong sense of community.

Get to Cinque Terre from France

We arrived in Italy from Nice, in the south of France.


  • Nice to Vintmille Station (50 mins)
  • Vintimille to Genoa (2 hrs 10 mins)
  • Genoa to Levanto (1 hr 10 mins)

Levanto is easily walkable. The train is not in the centre of town, and when we arrived at the station we were totally lost. It was a hot day, we were tired and we forgot to download our map (again). We eventually got a cab from the station to our accommodation. It wasn’t actually far away and if we’d known where we were going we could have walked.

Dog swimming in water in Levanto Italy

Accommodation in Levanto: Villa Clelia

A street back from the beach,  Villa Clelia was one of my favourite B&Bs on our trip. The rooms are small but clean and I loved waking up to our free, freshly-baked breakfast on our balcony every morning.

Day Trips to Vernazza & Monterosso, Cinque Terre

From Levanto, we did a day trip to two Cinque Terre villages, Monterosso and Vernazza. I’m so glad we took the ferry from Levanto to Vernazza because the view from the sea is spectacular!

Harbour in Vernazza Cinque Terre

Highlights in Cinque Terre

Of the five villages, Vernazza has the best streets for wandering. It feels a little bigger than the other villages, so there are plenty of opportunities to get lost wandering the streets. Well, not that lost. But it’s easier to escape the crowds here.

Vernazza was originally a fishing village and has a history dating back to 1080, when it was used as a naval base to defend against pirates. From the ocean, it was easy to spot the 15th century Doria Castle, built as a lookout for pirates.

A buttercup yellow bell tower overlooks the tiny harbour, which has water so clear that the boats look as if they’re floating on thin air!

Beach Monterosso Cinque Terre

Monterosso has the best beach in Cinque Terre. We started with lunch at a restaurant overlooking one of the beach clubs, which are very pretty with their brightly-striped umbrellas. When it came time for us to actually hit the beach, we went to the “Spiagga Libre”, or free beach, which was very crowded. While Chloe squished up on the sand among deeply-tanned Italians, I found some more elbow room in the bright blue water.

Beach in Monterosso Cinque Terre

Get around Cinque Terre

We took the ferry from Levanto to Vernazza. Afterwards, we took the ten-minute train from Vernazza to Monterosso. From Monterosso, it was another ten minutes by train back to Levanto.

Buy the Cinque Terre pass to get the best value.

We were lucky to board the small ferry at its first port in Levanto because at the next stop in Monterosso there was a horde of disappointed tourists who squished their way onboard, unable to find a seat and wobbling for the rest of the journey.

Riomaggiore, Cinque Terre (1 night)

We spent our final night in the region in the southern-most Cinque Terre village, Riomaggiore. Riomaggiore is the brightest of the town, and for that reason, my favourite.  From here, we visited Corniglia and Manarola.

Riomaggiore Seafood

Highlights of Riomaggiore

Riomaggiore is the most colourful place I have ever been. Shades of sunshine yellow, bright orange and watermelon pink punctuated by forest-green shutters shine even brighter against the brilliant blue sky.  Bright bunting strung across the main street made the town feel even more festive. We didn’t seek out particular sights but just enjoyed spending time in such a cheerful place.

Flags in Riomaggiore Cinque Terre

Get to Riomaggiore

Train from Levanto to Riomaggiore (around 20 minutes).

Accommodation in Riomaggiore

We stayed in Affittacamere Dune Blu, a gorgeous B&B on the main street in Riomaggiore. Bright, breezy rooms and a lovely host, Sarah. I would definitely stay here again.

Day Trip to Manarola & Corniglia, Cinque Terre

Highlights of Manarola & Corniglia

Manarola is the Cinque Terre village I’d been dreaming of. The colourful mosaic of pastel-coloured houses tumbling down the hillside to the edge of the water is best appreciated a little way along a footpath which leads to Corniglia.

Manarola Colourful View Cinque Terre

Corniglia was not my favourite. As in, it was my least favourite of the five. It is the only town not on the water, and when you arrive at the train station you can either walk up huge set of stairs zig-zagging up the mountain, or wait for a bus. It was the hottest day of our trip, so we waited for the bus – mostly so we could sit in air conditioning for ten minutes.

Corniglia Cinque Terre

It has a pretty centre, and has plenty of little laneways to explore and is surrounded by a pretty vineyard. I might have been a bit biased because we accidentally went to Corniglia on the first day too. Both times we went to the station, we managed to arrive when the trains had a break, so we were stuck waiting at the station for an hour, baking in sun. Not my fondest memories of the trip.

Get around Cinque Terre

Short train trips (5-10 mins) from Riomaggiore.

Milan (stop over) 

Milan is Italy’s financial and fashion capital. It’s a little short on tourist sights compared to other regional Italian capitals but I’d love to return to Milan and spend a few days getting under the city’s skin. Our two hour stop over was just enough time to see the city’s two major sights, the duomo and the galleria.

Galleria Vittorio Emanuele Milan

This stop only came up because of an odd train timetable the day we were meant to go from Cinque Terre to Florence

Highlights of Milan

Milan’s towering white duomo is one of the most magnificent buildings I have ever seen. Every inch is covered in ornate carvings. Unfortunately, we didn’t have time to walk along the top of the duomo – I’ll save that for next time!

In the same square is the beautiful Galleria Vittorio Emanuele II, one of the world’s oldest shopping malls. We walked through before going back to the train, and it’s beauty left a very positive image of Milan in my mind.

Galleria Vittorio Emanuele Milan

Get to Milan

We took a very early train from Riomaggiore to La Spezia, which is free when you have the Cinque Terre Card (10 mins).

We took the train from La Spezia to Milan (3 hrs 15 mins). Once we got to the station, we left our suitcases at a luggage storage facility at the station and took the Metro to the Duomo.

Verona (2 nights)

It’s the home of fabled, star-crossed lovers Romeo and Juliet, but there’s more to Verona than a Shakespearean tragedy.

Verona is a pretty, walkable city, centred on the River Adige. It’s just over an hour from Venice by train, so we decided to save money and stay in Verona for a couple of nights and do a day trip to Venice.

By doing this, we visited Verona, which we might not have done otherwise, and we had two nights in a row in one place.

Colourful building in Verona

Highlights of Verona

We ate in the Piazza delle Erbe, which was the town’s forum when it was ruled by the Roman Empire. Today, it’s fringed with somewhat touristy restaurants and filled with market stalls. There are some stalls worth looking at, but a lot of them are full of touristy trinkets.

We visited the courtyard of “Juliet’s house”, which was owned by the dell Cappello family in the 13th century. “dell Cappello” might not be a far cry from “Capulet”, but the famous balcony visited by thousands of tourists every year was added in the 20th century.

Markets Piazza in Verona Italy

We visited anyway since it was free and in the centre of town. We tried to find Juliet’s tomb, further outside the centre, but had no luck!

Romeo and Juliet might be pure fiction, but Verona still feels like a very romantic city. It’s a pretty place to wander through, which makes it a good one in my books!

Get to Verona from Milan

Train from Milan to Verona (1.5 hours)

Accommodation in Verona

We stayed in Ad Centrum Verona, great B&B in a popular student neighbourhood in Verona.  Be careful when you book – they have two locations in Verona, we went to the wrong one at first!

Day Trip to Venice

This was my second trip to Venice, after a trip a few years ago in winter. The summer season was a double-edged sword – the warmer weather was much more pleasant, but it was seriously overrun with tourists. Can’t complain, I was one of them!

Venice is a beautiful city, but after dark the city becomes a ghost town. Instead of getting the ferry to the main island in the morning and back to the mainland in the evening, we stayed in Verona.

I’m glad we took the evening train back to Verona, so we could spend two nights in a row in the same bed and enjoy another evening in a lively town.

Highlights of Venice

Yes, we went on a gondola ride. Yes, it was expensive. If you’re going all the way to Venice, I think it would be a shame not see it from its famous canals!

A 45-minute tour is 80 euros, regardless of how many people you have on the gondola. They will try and up-sell you to a longer (and more expensive) tour, but the 45 minutes was long enough for me.

Gondolier in Venice Italy

We ate lunch at a restaurant under the Rialto Bridge, with a great view of the hustle and bustle on the canals.

We spent some time wandering the streets and getting lost, did a bit of shopping and also visited St Mark’s Basilica – one of my favourite buildings in the world!

Rialto Bridge Venice

Get to Venice from Verona

We took a train from Verona to Venice. There are two major stations in Venice, go to Venezia Santa Lucia Station to make sure you arrive in the heart of Venice’s main island, rather than on the mainland.

The train takes 1 hour and 10 mins…providing you aren’t kicked off, like we were!

In a flurry of ticket booking, we accidentally booked our ticket from Verona-Venice for August, instead of September. We didn’t even notice until the ticket inspectors came around! We wasted about half an hour and 20 euros on a new ticket, at the Vincenza station. This was annoying, but at least we were already halfway there before we got caught!

 Restaurant on the water in Venice

Florence (3 nights)

This was my second time in Florence, but like Venice, I’d swapped winter for early Autumn. It had mild summer weather and had the crowds to match. Despite this, Florence was one of my favourite Italian cities of the trip, and I am definitely going to return for at least a week.

Duomo Architecture Florence

Get to Florence from Verona

Verona to Florence (1.5 hours). A nice direct trip!

Highlights of Florence

You can’t see it all in a few days, but you can see enough for a memorable visit.

We visited the sprawling, Renaissance-style Boboli Gardens, admired the Duomo, the bapistry and Giotto’s bell tower from the outside and walked along the beautiful, ancient Ponte Vecchio.

Ponte Vecchio Florence

With a long history of craftsmanship, Florence is a great city for shopping. Leathergoods and paper products are some of the city’s most traditional products. Madova makes beautiful gloves and El Papiro produces beautiful, traditional Florentine paper. Treat yourself!

Last time I visited Florence, I visited Piazza Michelangelo, which has beautiful views over Florence and saw the real statue of David in the Galleria dell’Accademia. This time, we settled for one of the copies, outside the Palazzo Vecchio, which is the town hall.

Gelato in Florence

Despite all my research before the trip, I didn’t know about the Gucci Museum and the Salvatore Ferragamo Museum. I am definitely visiting next time, along with the Uffizi Gallery!

Accommodation in Florence

We stayed in  Hotel Alessandra in Florence, which was so beautiful – especially considering our budget. The rooms are huge, the staff are lovely and the location can’t be beaten.

Rome (4 nights)

I have to admit, Rome is not my favourite Italian city. 

Despite this, I’ve always found it worth visiting.

Traffic in Rome

We had one night in Rome before our Contiki Tour started, then had three nights on tour. When we arrived in Rome, I was regretting booking a tour, but our guide, Maite, was so brilliant that I have no regrets.

Maite is a local, which really added SO much to my trip. I loved her walking tours and how she brought Rome’s history to life. Wherever I travel from now on, I’m always going to book a tour with a local guide!

It’s also a great way to support people who put so much time and effort into studying their city and keeping its history alive.

Spanish Steps in Rome

Highlights of Rome

This was my second visit to Rome, so I didn’t join our tour when they visited the Colosseum or Vatican City, instead taking a morning off to catch up on sleep and eat lunch at a local restaurant.

I visited the Trevi Fountain again, which was the usual crush of tourists. This time, we did an Italian cooking class, which was probably my favourite part of visiting Rome – oh, and eating all the pizza, pasta and gelato that came way.

Eating pizza in Rome

Last time I also visited the Crypt of the Capuchin Monks. It makes the catacombs of Montparnasse in Paris look like a walk in the park! This crypt is very creepy, featuring small galleries of “art” made by Capuchin Monks…using human skulls and bones, remnants of a devastating plague.

Creepy, but definitely memorable.

Get to Rome from Florence

Train from Florence to Rome (1 hour 20 mins). Rome’s Metro stops are few and far between, and the trains were often delayed or on one day, not running at all. Pick an area to explore, Rome is not an easy city to aimlessly wander.

Tiny car in Rome Italy

Accommodation in Rome

We stayed at the Regent Hotel Rome. This was where our tour started, so we didn’t choose this accommodation however the rooms were very comfortable and the hotel was in a nice part of town. Because Rome’s metro system is pretty shocking and it is a huge city, I would stay much closer to Piazza Navona next time. I personally prefer smaller hotels and B&Bs that are owner-managed and where you feel more like a personal guest.  But that just might be me! I know some people prefer the anonymity of bigger hotels which feel more familiar.

Sorrento (3 nights)

We were in Sorrento as a cheaper base for visiting Amalfi and Capri. It’s quite a pretty place, but perhaps not as charming as other Italian riviera towns. We might have been a little biased, as the mood was sombre after 70% of our group had their stuff stolen at La Reggia Designer Outlet, just outside of Naples.

Slow food margarita pizza in Sorrento

Highlights in Sorrento

I ate lots of great food here, visited a cheese-making demonstration not too far from town and also had sandals custom made!

La Conchiglia is a small workshop where you can choose the sandal design and colour. The shoe maker made the sandal so that it would be comfortable despite my narrow ankles (his diagnosis) and he was pretty quick at putting them together. I love them and they are one of my favourite souvenirs!

Get to Sorrento

We arrived by tour bus. The centre of Sorrento is small, so we walked everywhere.

Accommodation in Sorrento

We stayed at Giosue A Mare Hotel in Sorrento. The hotel rooms are tiny but clean, but the staff were a little cold (or sometimes downright cranky). It had a nice location by the water, but there were a lot (A LOT) of stairs between the hotel and street level. There was an elevator, which charged a couple of Euros.

Day Trip to Amalfi & Positano 

The crown jewels of the Italian Riviera, the tiny towns of Amalfi and Positano are just as charming, crumbling and packed with tourists as you’d expect of such legendary holiday hotspots.

Visiting on a day trip suited our budget perfectly. They’re very small and very busy so I was happy to spend the day there but return to the quiet town of Sorrento at night.

Beach in Positano Italy

Highlights of the Amalfi Coast

Driving the along the famous Amalfi Coast was exciting and beautiful – but admittedly, not as jaw-dropping as I had expected.

While we were in Amalfi, we treated ourselves to a lemon cream pie from Andrea Pansa, the famous local patisserie. The Amalfi Cathedral is ancient and beautiful, overlooking the main square in Amalfi.

Foot massage on Amalfi Beach

I also indulged in a foot massage at the beach. I paid, before remembering that I’m the most ticklish person in the world. At first, it was hard not to kick the masseuse and dissolve into giggles, but I eventually relaxed and enjoyed it!

The beach at Amalfi is grey and most of it was roped off by an ugly metal metal fence. The town of Amalfi is very pretty, but the beach….not so much!

Getting around the Amalfi Coast

Our tour group hired a special Amalfi Coast bus driver to drive along the treacherous yet beautiful scenic Amalfi route. He dropped us in Positano, which is where we caught the ferry to Amalfi.

Day Trip to Capri 

The isle of Capri, like most of the Italian Riviera is tiny, beautiful, expensive and crawling with tourists. I’m so glad I visited because it was so beautiful but I’m glad I didn’t stay on the island. It’s too crowded!

Sailing around Capri Contiki

Highlights of Capri

We spent half the day sailing around Capri which was the most blissful travel experience of my life. We soaked up the sunshine while the skipper shared the history and local legends of the island, and took us to the Green, White and Blue Grottoes. Crawling into a dinghy and entering the Blue Grotto, a cave where the water glows a bright, deep blue, was a surreal and unforgettable experience.

Back on dry land, we took the funicular up to Anacapri, to each lunch at Il Verginiello, visit the lush gardens, eat more gelato and shop at the famous Carthusia parfumerie, one of the oldest in the world. The scents were developed by monks, which might explain why they were somewhat repellant. I settled for a lemon-scented candle.

White Grotto Capri Italy

Get to Capri

The ferry to Capri was right near our hotel and it took around 40 minutes. It’s a bit of a bumpy ride!

Day Trip to Pompeii

My mum always talks about how much she loved seeing Pompeii when she travelled in her 20s, so I was really excited.

Unfortunately, I woke up the morning we were going to Pompeii, the serious back and neck pain. It was so bad, I every step was agony. It was totally self-inflicted because I had been naughtily hauling around an over-stuffed suitcase for weeks – lesson learned!

As a result, I didn’t enjoy Pompeii quite as much as I would have otherwise, but I still remember being amazed at the technology these people had and how advanced they were. It’s a really interesting one-hour tour – you won’t see all of Pompeii, that takes about five days!

Get to Pompeii

This was part of my tour, so we arrived by bus.

Bari – on to  Greece!

Our bus drove us to the port at Bari, where we took an overnight ferry to Piraeus in Greece. Once we arrived in Greece, it was around a whole day’s driving to get across the country to Athens. If you’re travelling independently you might want to look for a stopover in between to see somewhere new, or fly.

Have you been to Italy? Is it on your list?

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Itinerary 2 weeks in Italy

Itinerary 2 Weeks in Itay

21 thoughts on “Itinerary: 2 weeks in Italy

    1. You’re welcome! I’ll have to check out your latest blog post, I’m planning to go to Japan later this year!

  1. Great report on your trip! I was curious to learn more about the tour guide experience with Maite. How did you find out about her?

    1. Maite works for Contiki Tours, so I was on an Italy tour when she was my guide. Unfortunately, you can’t pick your guides with Contiki, it’s luck of the draw! I’ve travelled with them twice and have had very knowledgeable guides both times 🙂

  2. how much did this cost in total for trains hotel flights and petrol etc. me and my girlfriend are planning to do 2-3 weeks trip in italy and this is perfect!

    1. Hi Eros, trains were quite cheap, usually less than $50. You can book online and look quite far in advance to get an idea of exact prices for the time of year you’re planning to go. Accommodation was about 100 euro per night, for a room in a B&B or small hotel. The great thing about Italy is that wonderful hospitality is part of their culture, so you don’t need to spend big bucks to get great service. We didn’t fly around Italy and any driving was done on a tour bus, in the second part of the trip, as part of a longer tour through Italy/Greece. Trains are the way to go if you’re travelling by yourselves.

  3. If you don’t mind me asking, about how much did you spend during your two week trip to Italy? Thank you 🙂

  4. Great post! My friends & I did a 10-day tour of Northern Italy last summer. Our itinerary was very similar except we did Pisa & Riccione instead of Rome, Pompeii, Sorrento, Amalfi & Capri. Cinque Terre was magical, definitely my favourite stop on that trip – can’t wait to go back!

    1. Wow, sounds amazing! Yeah it’s hard to even believe that somewhere like that exists, it is so different to anything I’d ever seen before. Thanks for commenting, was great to hear from you 🙂

  5. Amazing itinerary! I had a huge trip planned to Italy for September, I had a similar itinerary, but we would go until Sicily and we would drive from Germany… unfortunately we had to cancel our trip as it was too expensive for us at the moment and we decided to go to Turkey for about 2 weeks, and dive 🙂 maybe one day we will do this trip! I guess you guys had lots of fun! Where would you like to have spend more time?

    1. Thank you! That’s a shame about your trip but two weeks in turkey would be amazing!! My trade off was I could go to ancient Ephesus in turkey but couldn’t afford to see Istanbul. I would have liked more time in Levanto 🙂 so relaxing! Or one more day in Florence, it’s such a great city

      1. Yes I know…but Im really happy about Turkey, always wanted to go there, but didnt when, it ended up happening now 😀 Ohh nice, I’ve been to Florence before, but not Levanto!! 😀

  6. Verona captures the heart, doesn’t it? I absolutely loved Venice when I was there. But I didn’t get to spend as much time in Italy as a whole like I wanted .That’s what going back is all about.

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